From Boardwalk to Bank: Jackie Reses' Rise in Fintech

Jackie Reses' journey from a "pretty gritty childhood" in Atlantic City to the top of the U.S. fintech industry is a testament to her entrepreneurial spirit and strategic acumen. Born into a family of entrepreneurs, Reses' early experiences running carnival games on the boardwalk instilled in her a strong sense of self-reliance and a desire to succeed. This foundation would later shape her leadership style and approach to business, particularly in the fintech sector.

Reses' entrepreneurial journey began in earnest during her college years at the University of Pennsylvania's Wharton School, where she ran custom t-shirt and taxi businesses. These ventures honed her leadership principles and learning style, which she credits to her early career at Goldman Sachs. Handling mergers and acquisitions for the firm, Reses developed a strong foundation in finance and business strategy. This experience was critical to her leadership style, as she later mentioned that many of her leadership principles were set during her time at Goldman Sachs.



Her entrepreneurial spirit and leadership style were further refined during her tenure at Yahoo, where she played a key role in resolving the "toxic" relationship with Alibaba. This experience was life-altering for Reses, as she worked with Alibaba co-founders Jack Ma and Joe Tsai to separate out Alipay and assist with Alibaba's initial public offering. She described the experience as "an amazing experience" that drove her to question assumptions about how to operate a company. This ability to navigate complex relationships and drive significant business outcomes has been a hallmark of her leadership style.

At Square, Reses applied her entrepreneurial roots and her experience in building products that challenged every convention of banking and lending. She described this as a business that hadn't existed in a tech company before, and she wanted to build products that challenged every convention of banking and lending. This experience led her to want to own a bank, a goal she accomplished in 2022 when she bought a community bank based in Kansas City, Missouri, and transformed it into the current Lead Bank, which now also provides infrastructure to fintech companies.

At Lead Bank, Reses plans to continue her work transforming banking by boosting the bank's existing business lines, which include serving consumers, businesses, and fintechs through banking-as-a-service. She said, "The business lines that Lead Bank is in today are serving consumers, serving businesses and serving fintechs through banking-as-a-service, and I think we’ll continue to do the same thing. But we’ll have additional technical, regulatory and compliance expertise that we can add in to make the experience hopefully better for our customers." This strategic decision is influenced by her experience at Goldman Sachs, where she learned the importance of technical, regulatory, and compliance expertise in building a successful business.

Reses' experience working with global tech giants like Alibaba and Square has significantly influenced her vision for Lead Bank and brought unique perspectives to the fintech sector. Her time at Alibaba, for instance, was a "life-altering experience" where she worked closely with co-founders Jack Ma and Joe Tsai. This exposure to a different culture and way of doing business, from operations to HR policies, drove her to question assumptions about how companies operate. She noted, "Seeing a different culture and a different way of doing business, from operations to HR policies, to how you set up a bank, to separation of corporate ownership. I was being driven to question assumptions about how you operate a company. It was an amazing experience." This experience has likely shaped her approach to innovation and operational efficiency at Lead Bank.

At Square, Reses played a pivotal role in transforming the company into a financial services powerhouse. She joined Square in 2015 as the capital lead and executive chair of Square Financial Services, a time when the company was still relatively small. Reses described this period as a return to her entrepreneurial roots, where she built banking and lending products from the ground up. She stated, "I thought it would be super fun to go build out banking and lending for Square. It really was a business that hadn’t existed in a tech company, and I wanted to build products that challenged every convention of banking and lending, and really turn the business on its head." This hands-on experience in building a fintech infrastructure from scratch has given her a deep understanding of the challenges and opportunities in the sector, which she now applies to Lead Bank.

Reses' unique perspectives include a strong focus on customer service and technology. At Lead Bank, she aims to leverage her vast resources and business connections in global technology and finance to enhance the bank's offerings. She plans to continue serving consumers, businesses, and fintechs through banking-as-a-service, but with additional technical, regulatory, and compliance expertise. She said, "We’ll have additional technical, regulatory and compliance expertise that we can add in to make the experience hopefully better for our customers. So I think we already have a breadth of product lines we can lean into with additional technical expertise and legal and compliance expertise, and we can hopefully serve people with additional technology they haven’t experienced before." This approach reflects her belief in using technology to improve financial services, a perspective honed during her time at Square and Alibaba.

Moreover, Reses' experience with Alibaba and Square has instilled in her a deep appreciation for the importance of community and small businesses. Growing up in a family of entrepreneurs in Atlantic City, she developed a soft spot for small business owners. This, combined with her experience at Alibaba and Square, has shaped her vision for Lead Bank as a small business powerhouse. She plans to use her new position as chairwoman to help small businesses as much as possible, reflecting her entrepreneurial background and her belief in the importance of community.



In conclusion, Jackie Reses' journey from a "pretty gritty childhood" to the top of the U.S. fintech industry is a story of entrepreneurial spirit, strategic acumen, and a deep appreciation for community and small businesses. Her experiences at Goldman Sachs, Yahoo, and Square have shaped her leadership style and approach to business, and her vision for Lead Bank reflects her belief in using technology to improve financial services and support small businesses. As she continues to transform banking at Lead Bank, Reses' unique perspectives and strategic decisions will likely continue to drive the bank's success and influence the fintech sector.